High‐field <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy of some corticosteroids and related compounds

Duddeck, H.; Rosenbaum, Doris; Hani, M.; Elgamal, Abdelbaset M.; Fayez, M. B. E.

doi:10.1002/mrc.1260241113

Cited by 26 publications

(7 citation statements)

References 28 publications

(1 reference statement)

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“…Oxidation of 3--hydroxypregn-5-en-20-one (1c, 119 mg, 0.376 mmol) with 3 (1.8 mg, 0.0019 mmol) and K2CO3 (5.2 mg, 0.0376 mmol) in acetone (3 mL, containing 0.6% of water) for 24 h gave 96 mg (81%) of the product after flash chromatography (CH2Cl2/ether, 10:1). The product was characterized by comparison with an authentic sample: 22 …”

Section: Methodsmentioning

confidence: 99%

Ruthenium-Catalyzed Oppenauer-Type Oxidation of 3β-Hydroxy Steroids. A Highly Efficient Entry into the Steroidal Hormones with 4-En-3-one Functionality

1996

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Oxidation of 5-unsaturated 3beta-hydroxy steroids 1 to the corresponding 4-en-3-one derivatives 2 can be performed efficiently by acetone at reflux in the presence of a catalytic system consisting of either (PPh(3))(3)RuCl(2) (3) and K(2)CO(3) or [(C(4)Ph(4)COHOCC(4)Ph(4))(&mgr;-H)][(CO)(4)Ru(2)] (4). The reaction proceeds via a ruthenium-catalyzed dehydrogenation of 1 and subsequent hydrogen transfer to acetone with concomitant double bond migration.

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Section: Methodsmentioning

confidence: 99%

Ruthenium-Catalyzed Oppenauer-Type Oxidation of 3β-Hydroxy Steroids. A Highly Efficient Entry into the Steroidal Hormones with 4-En-3-one Functionality

1996

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“…spermine). 1 H NMR analysis of all the conjugates confirmed the presence of the 3-enone and, if the parent steroid molecule had them, 11-OH and 17-OH groups [21][22][23][24][25], as well as 1 H signals from the conjugated spermine and the 21-αketo thioether group. NMR evidence of conjugation was visible by the methylene hydrogens on the iminothiolane linkage adjacent to the amidine (δ = 3.38), the methylene hydrogens on the spermine (δ = 3.12) and the protonated amine on the amidine (δ ∼ 6.4).…”

Section: Synthesismentioning

confidence: 78%

Synthesis and structure‐activity relationships of a series of increasingly hydrophobic cationic steroid lipofection reagents

Gruneich

Diamond

2007

The Journal of Gene Medicine

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The use of cholesterol-based cationic lipids and the ability of glucocorticoids to reduce local inflammatory response to lipoplexes motivated an investigation of structure-activity relationships for cationic steroids. A one-step synthetic scheme using iminothiolane was developed to link spermine to the 21-OH position of steroids via an amidine linkage. Five steroids (cortisol, dexamethasone, corticosterone, 11-deoxycortisol, and 11-deoxycorticosterone) with increasing hydrophobicity of the parent steroid (Log P(ster) from 1.51 to 3.01) were conjugated with spermine, formulated with dioleoylphosphatidylethanolamine (DOPE) at DOPE : steroid mole ratios (R) of R = 0.5 to 2, and then complexed with 1 microg enhanced green fluorescent protein (EGFP) plasmid DNA at charge ratios (CR) = 2 to 24 amines per phosphate (0.5 to 6 steroids per phosphate). The resulting 105 different formulations of the cationic steroid series were used to lipofect bovine aortic endothelial cells. Transgene expression data at either 24 or 48 h post-lipofection for all formulations was collapsed onto master curves when plotted against a single empirical dimensionless parameter, the lipofection index (LI) = CR (Log P(liposome))(Log P(ster)/|DeltaLog P|) [R/(R + 1)] where DeltaLog P = Log P(DOPE)- Log P(ster) and Log P(liposome) is a mole-weighted average of the DOPE/cationic steroid liposome hydrophobicity. For 7 < LI < 29, the EGFP expression at 24 or 48 h post-lipofection increased linearly with LI (EGFP approximately 0 for LI < 7), but did not increase further for LI > 29, thus providing a predictive design rule based on Log P of the hydrophobic moiety of the cationic steroid lipid.

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“…showed that logP have a correlation with the passive diffusion from some steroids. Additionally, several studies 15,16 have determined the relationship of some steroid derivatives with the physicochemical descriptors such as logPπ, R m , V m and the frontier molecular orbitals (HOMO-LUMO gap) 17,18 . All these works show several protocols for QSAR study of steroids that involved; geometry optimization, conformational analysis and electronic energy.…”

Section: Whichmentioning

confidence: 99%

Synthesis of Two Steroids Derivatives and its Relationship with some Physicochemical Parameters

Figueroa‐Valverde

Díaz-Cedillo

Elodia

2011

Journal of Chemistry

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Two danazol derivatives were synthesized and characterized by spectral analyses. In order to characterize the structural and physicochemical requirements of danazol derivatives, several parameters such HOMO-LUMO gap, ΔHf, RMSg, dipole moment (µ) and bond length were evaluated. The results showed that HOMO and µ was high in the compound 5 in comparison with the compound 3. In conclusion all these data indicate that increase in the length of chain induce greater moment dipole and increase HOMO gap in the compound 5 with respect to 3.

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High‐field ¹H and ¹³C NMR spectroscopy of some corticosteroids and related compounds

Cited by 26 publications

References 28 publications

Ruthenium-Catalyzed Oppenauer-Type Oxidation of 3β-Hydroxy Steroids. A Highly Efficient Entry into the Steroidal Hormones with 4-En-3-one Functionality

Ruthenium-Catalyzed Oppenauer-Type Oxidation of 3β-Hydroxy Steroids. A Highly Efficient Entry into the Steroidal Hormones with 4-En-3-one Functionality

Synthesis and structure‐activity relationships of a series of increasingly hydrophobic cationic steroid lipofection reagents

Synthesis of Two Steroids Derivatives and its Relationship with some Physicochemical Parameters

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High‐field 1H and 13C NMR spectroscopy of some corticosteroids and related compounds

Cited by 26 publications

References 28 publications

Ruthenium-Catalyzed Oppenauer-Type Oxidation of 3β-Hydroxy Steroids. A Highly Efficient Entry into the Steroidal Hormones with 4-En-3-one Functionality

Ruthenium-Catalyzed Oppenauer-Type Oxidation of 3β-Hydroxy Steroids. A Highly Efficient Entry into the Steroidal Hormones with 4-En-3-one Functionality

Synthesis and structure‐activity relationships of a series of increasingly hydrophobic cationic steroid lipofection reagents

Synthesis of Two Steroids Derivatives and its Relationship with some Physicochemical Parameters

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High‐field ¹H and ¹³C NMR spectroscopy of some corticosteroids and related compounds